This invention relates to a class of quinoline-5,8-quinones (also called 5,8-quinolinediones), which are useful for the therapy of immediate hypersensitivity reactions and conditions characterized by excessive release of slow-reacting substances or leukotrienes. This invention also includes a method for treating the above conditions, which comprises administering to animals, including humans, an effective dose of the quinoline quinone compounds.
Various 6-substituted-quinoline-5,8-quinones have been prepared by those skilled in the art; however, the references describing these preparations do not teach the use of the compounds as inhibitors of leukotriene release. For example, Long, R. and Schofield, K. in "Some Properties and Reactions of Quinoline-5:8-quinones", J. Chem. Soc., 3919-3924 (1953) describe the preparation of 6-substituted quinoline-5,8-quinones, in which the 6-position substituent can be: hydroxy, halo, alkyl, anilino, or hydrogen. Long and Schofield indicate that antimalarial action and bacteriostatic properties are expected, whereas the quinones taught herein are useful in treating excessive release of leukotrienes.
Antibacterial properties are described for 6-methyl and 6-anilino-quinoline-5,8-quinones in Petrow, V. and Sturgeon, B. "Some Quinoline-5:8-quinones", J. Chem. Soc., 570-574 (1954). Other substituted quinoline-5,8-quinones are described in: Pratt, Y. T. "Quinolinequinones, VI. Reactions with Aromatic Amines", J. Org. Chem., 27, 3905-3910 (1962); Pratt, Y. T. and Drake, N. L. "Quinolinequinones. II. N-Substituted 6-Amino-5,8-quinolinequinones", J. Amer. Chem. Soc., 77, 37-40 (1955); and Pratt, Y. T. and Drake, N. L. "Quinolinequinones. V. 6-Chloro- and 7-Chloro-5,8-quinolinequinones", J. Amer. Chem. Soc., 82, 1115-1161 (1960).
A copending application, Ser. No. 429,589, filed Sept. 30, 1982, describes a class of isoquinoline quinones, while another copending application, Ser. No. 430,896, also filed Sept. 30, 1982, describes a class of quinoxalinedinones. Both applications teach the use of the compounds to inhibit the release of leukotrienes and to treat immediate hypersensitivity reactions, such as asthma.